Who's Whose Who?
by KAHOPEd00l
Summary: Will and Grace have both been hiding their new relationships from one another. As their respective romances become more serious, will they be able to keep them under wraps? After all, secrets can only stay secret for so long. Grace/Karen & Will/Jack.
1. Chapter 1

Author's Note:

This story is obviously not canon, but I don't know if I would consider it a real AU either. In my head, it takes place somewhere around Season Three or Season Four in terms of the looks/ages of the characters as well as their various character and relationship development. I don't think that anything like this would ever happen on the show (but I would love if it did lol) but this idea popped into my head and wouldn't leave until I wrote the story. I wouldn't necessarily consider anything featured in this story to be smut but there are definitely some intimate moments, innuendo, and a bit of language so I decided to play it safe with a "T" rating. The entire story takes place over the course of one week but you only see the first three days and then the seventh and final day which is broken up into three chapters. I hope you all enjoy it.

Side Note: Treat the line breaks as if they were jump cuts between different scenes.

*** Disclaimer *** I don't own any of the rights to the show Will & Grace or the characters featured in this story. All rights belong to the creators, writers, and producers of this Will & Grace.

* * *

Chapter One:

Day One:

"Alright, sweetie, I'm headed out now and I probably won't be back until really late so don't wait up," she heard him call.

"Okay, have fun," she responded from her place on the couch in front of the television.

As soon as she heard the door close, Grace jumped up and ran toward her bathroom. She began to get ready and as she looked in the mirror and applied her makeup her mind drifted back to the question that she had been asking herself for the last three months. Should she tell him? He was her best friend and she wanted to believe that he would be happy for her, but she just couldn't ignore that nagging feeling that he wouldn't be able to understand. Hell, she wasn't sure that she understood but she had given up trying to figure _that_ part out weeks ago.

She gave herself the once over in the mirror and decided that it was good enough. She moved toward her room where the new dress that she had bought was laid out on her bed, ready to impress her date. Wondering what kind of response her much-too-expensive-but-impossibly-sexy-and-irresistible purchase would garner gave her butterflies.

She put the final touches on her look with some simple jewelry and a nice pair of nude sling-backs. Just as she was about to walk out the door to meet her date the doorbell rang. Grace answered the door and was surprised to see Karen standing on the other side.

"Hi," Grace said, "what are you doing here?"

"Listen, honey, I know that we agreed to meet at the manse, but we can't."

"Why not?"

"Well, I told Gardner a couple of weeks back that I would pay for his cousin's plane ticket to America if he smuggled in some pills for me. Well, turns out that the genius smuggled them in inside some kind of stuffed animal that was infested with some sort of bug and now the manse is crawling with them. I'll tell you, it's a good thing I downed a few of those happy pills before I found out or I'd have really lost it," she chuckled.

"Oh, my God, that's awful! But why didn't you just call and tell me?"

"Because I figured if I called, you would've just cancelled, and I wanted to see you." She paused as she pulled a bottle of champagne and held it up, "But I brought the good times with me, so we can just have our date here."

"Karen," Grace sighed, "You know that we agreed not to meet here. It's too risky. Will or Jack could see us and figure out what's going on – "

"And remind me again why we don't want that."

"Karen," Grace said in a frustrated tone.

"Alright, alright, honey, I know you're not ready to tell Wilma yet. It's okay. But from what I can see, he's not here right now and you look incredible in that dress so why don't you let me in," Karen said as she reached out her hand and allowed one finger to trace Grace's arm from her shoulder all the way down to the tips of her fingers before hooking Grace's hand into her own.

Karen's action caused Grace to get goosebumps all over her body, and her brain shouting at her to say the hell with it and drag Karen into her bedroom sufficiently drowned out the other voice telling her that this whole thing was a bad idea.

"Okay, you can come in. But only this once and only because I know for a fact that Will is going to be gone for a while. He and Jack went to some club to cruise for guys, so they should be gone for a few hours at least."

"A few hours is better than nothing," Karen said happily as she entered the apartment.

As Karen walked past her, Grace tugged on her hand which was still intertwined with her own causing Karen to stumble into her body. The two of them met eyes and paused for a moment before leaning in and allowing their lips to meet. It was a short but powerful kiss. One that showed their level of ease and comfort with one another but also conveyed the passion that was simmering just beneath the surface.

"Hi," Grace said as she let out a breath.

"Hi," Karen answered back with a smile that mirrored Grace's.

* * *

They had started out with every intention to have a nice dinner together but while they were waiting for the pasta water to boil they had made the mistake of sitting down next to one another on the couch and one thing led to another which is how they now found themselves on top of Grace's bed making out like teenagers.

Grace felt her toes curl as Karen kissed down her neck and hit that spot behind her ear that only she had been able to discover. The next thing she knew, Karen had managed to unzip her dress and was pulling it down her body.

"Gracie, as beautiful as you look in this dress and as much as I can't wait to see you in it again, it has to go for now," Karen mumbled as she placed kisses across Grace's body.

Grace allowed Karen to continue the assault on her senses for a few seconds more before she decided that it was time to level the playing field and used her leg to flip Karen over. She leaned her head down to kiss the shocked look off of Karen's face as she threw her leg over top of her and sat down on her thighs. Grace pulled off Karen's skirt and allowed her chest to drag against Karen's legs as she slowly made her way back up her body and began unbuttoning her shirt, placing a kiss on each newly exposed inch of skin. When she made it to the last button she pulled the shirt open to expose Karen's midriff, then leaned down and gently bit on the skin above Karen's right hip.

Inspired by Grace's playful actions, Karen decided to return the favor and flipped them over once again returning Grace to her previous position. Grace let out a startled laugh and reached up to pull Karen's face down to hers. Karen found herself completely lost in kissing Grace before snapping back into reality and pulling away.

"Stop distracting me," Karen said as she began to move down Grace's body once again.

This time she made sure that she was sitting directly on top of Grace's legs rendering her unable to flip them again. She placed both of her hands on Grace's shoulders and ran them down her arms until she was able to lace their fingers together. As she took one of Grace's breasts into her mouth, she felt the red-head squeeze her hands tightly. Karen repeated the action on the other side before leaving a trail of open-mouthed kisses down her abdomen until she reached the top of Grace's underwear. Taking the edge of the material between her teeth, Karen began to pull the garment down Grace's legs. She got them down to her knees before releasing Grace's hands and continuing the crawl backward with them in her mouth until they slipped over Grace's ankles and off of her feet. She sat back and opened her mouth, releasing the underwear with a self-satisfied smirk on her face.

"Holy crap," Grace said, "That was really sexy."

"Well, honey, if you thought that was sexy, then you're really going to love this," Karen responded as she parted Grace's legs and leaned down to begin placing kisses back and forth from one side to another while working her way back up her body.

Just then they heard the front door open and the distinct sound of two men's voices. Karen froze as Grace shot up and threw her robe on. Grace couldn't understand what they were saying but she was sure that the voices belonged to Will and Jack. She felt a panic rise up within her and she motioned to Karen to get dressed.

"Oh, my God! Oh, my God! Oh, my God! Will and Jack are here," she whispered, "what are we going to do? See, I knew this was a bad idea! I knew we were going to get caught! Oh, my God!"

"Okay, relax," Karen whispered back, "they have no idea that I'm here. They probably don't even know that you're here. You're supposed to be out on a date, remember?"

"Right! Okay, so we can just say that my date was cancelled. But that doesn't explain why you're here. Or why you're in my room. No, you know what, we need to figure out a way to get you out of here without them noticing you," Grace paused as she tried to think of something, "Okay, here's what we're going to do. I'm going to go out there and create a distraction and you're going to sneak out."

Before Karen could even respond, Grace was closing the door behind her as she walked out toward the living room.

* * *

"Hey, guys," she called out to Will and Jack who were deep in conversation on the couch and seemed to be very startled by her sudden appearance.

They both jumped about five feet in the air before Will said,

"Hey, what are you doing here? I thought you had a big date?"

"Oh, you know, I started to feel a little queasy, so I had to reschedule it for tomorrow night. I'm fine now, though. What are you two doing back so soon?"

"Well, you know how clubs are. It's fun for a little while but then it gets too crowded," Will said.

"Plus, it was all young guys in their early twenties and they kept requesting all of these new Madonna songs, so we decided to just come home to watch Evita and re-live the glory days," Jack added.

Something about Jack being anything less than ecstatic about a club full of younger men seemed a bit off to Grace, but she was too panicked to really think about it.

"Oh, fun. But you know, there was something weird going on with the T.V. earlier," Grace tripled the volume of her voice before continuing, "why don't you guys come over here into the T.V. room and look at it."

Grace led the two men directly to the T.V. where she desperately tried to convince them that something was wrong with the picture.

"I don't know, Grace," Will said, sounding a bit worried, "I don't see anything wrong with it. Are you sure you're okay because you're acting really weird."

"Yeah, I'm fine but I swear the picture was off earlier."

"Something is off, that's for sure," Jack said impatiently.

"Well, if you're sure that it looks fine to you then I'm just going to head back to bed," Grace said to Will, completely ignoring Jack and praying desperately that she had bought Karen enough time to sneak out of the apartment.

"Okay, you do that. Goodnight, sweetie," Will said.

"Goodnight," Grace replied as she walked back through the living room toward the hallway.

As she entered her room, she breathed a sigh of relief that turned into a yelp of shock when she saw Karen still perched half-naked on her bed with a big smile on her face.

"Grace, are you okay," Will's voice called.

"Um, I'm fine. Goodnight," she yelled back before she lowered her voice into an angry whisper and said, "Karen! Why are you still here? I gave you more than enough time. You were supposed to leave!"

"Gee, honey, I know but the thing is, well, I just didn't want to," Karen said in her best cutesy voice as she adopted a sad puppy face.

"Oh, Karen," Grace exclaimed with obvious frustration.

Karen crawled toward the edge of the bed and reached out to grab on to the belt of Grace's robe. Once she had it in her grasp, she gave it a gentle tug and Grace allowed herself to tumble onto the bed.

"I'm sorry, Gracie, I just wanted to spend the night with you," Karen said with a sincerity that melted Grace's heart a bit.

"Okay, okay," she sighed, "You can stay as long as you promise to be up and out before Will wakes up in the morning."

"I promise," Karen said as she leaned down to place a kiss on Grace's lips.

"And no funny business either! I don't need anyone overhearing the two of us in here."

"Well, that promise will be a little harder to keep but I will try. I know how hard it is for you to be quiet," she said with a wink.

"Me," Grace exclaimed, "You're one to talk."

"Take it as a compliment, honey. When you're good, you're good."

Grace rolled her eyes as she extracted herself from the tangled mess of limbs her less-than-graceful collapse onto the bed had caused. She crawled up toward the headboard and pulled the covers back before motioning for Karen to join her. Karen complied happily with Grace's request and the two of them snuggled up next to one another under the blankets. Karen sat up ever so slightly and turned to give Grace a goodnight kiss but before their lips could make contact Grace said,

"What did I say? No funny business!"

"I was just trying to say 'goodnight'," Karen replied, a little hurt.

"Good night. Now go to sleep and remember, you have to be out of the apartment before Will wakes up."

"I know," Karen paused and allowed the silence of the night to wash over the room before she gave voice to the little fear inside her and timidly asked, "You aren't really mad at me, are you, Grace?"

Hearing the slight tremble in Karen's voice and sensing her vulnerability immediately erased any of the slight annoyance that Grace might have felt a moment before and as she reached down and laced her pinky through Karen's she replied,

"No, I'm not really mad."

Karen allowed herself to be satisfied with that answer for just a moment before she decided to ask the question that she had been terrified to ask for months.

"Gracie?"

"Yeah?"

"Are you happy?"

As Grace felt the love bubble up within her, she turned onto her side and looked Karen directly in the eye before answering,

"Yes."

This time it was Grace who leaned forward for a kiss and Karen was more than happy to accept it. They snuggled closer together and fell into a peaceful sleep in one another's arms.


	2. Chapter 2

Chapter Two:

Day Two:

Will was awakened by an arm falling across his torso and as he opened his eyes a smile spread across his face at the realization that it was Jack's. He allowed himself a moment to indulge in the simple pleasure of lying in bed next to the man that he loved before giving Jack's hand a gentle squeeze and then tapping it twice so as to indicate that he needed him to move his arm and allow him to get up.

After he had finished getting dressed for work, Will sat down on the edge of the bed and put on his shoes. The light jostling seemed to rouse Jack from his slumber and he rustled for a minute before fully waking and then smiling as he made eye contact with Will.

"What time is it," he asked groggily.

"It's early," Will whispered as he leaned down to give him a quick peck, "Go back to sleep and I'll see you later tonight. I was thinking, since Grace is going to be out tonight, maybe we could just have a nice romantic dinner here."

"Sounds great," Jack replied.

"Okay, it's a date then. And remember, you have to stay in here until after Grace leaves for work."

"I know, I know," Jack said impatiently. "Have a good day at work. I love you."

Will leaned down to place another kiss on Jack's lips and then replied,

"I love you, too."

He turned to exit the room and smiled to himself as he heard Jack begin to snore lightly before he even reached the door.

* * *

It took only a split second for Will to become aware of his surroundings. The theme of Moonstruck played repeatedly on the T.V. as the movie had clearly been over for some time and had returned to the main menu, there were the remnants from dinner still on the kitchen counter, a bowl of popcorn sat on his lap, and the weight he felt on his shoulder was due to Jack's head laying upon it. In the next split second, Will was able to gather what it was that had woken him out of such a sound sleep – the sound of keys jangling as they hit the floor in the hallway and the sound of Grace's voice as she cursed them out.

Looking back later, Will surmised that he probably could have just woken Jack up, told him to play it cool, and acted like the two of them had just been hanging out and watching a movie like they had a million times before. But in that moment, his guilty conscience, caused by having lied to his best friend every day for the last two and a half months, took over and he went into panic mode.

He shook Jack awake, yanked him up from the couch, dragged him through the living room, shoved him through the doorway of his bedroom, and slammed the door just as Grace walked into the apartment.

"Hey, sweetie," he said a little too enthusiastically as he walked back into the living room.

His enthusiasm didn't seem to faze Grace as much as the fact that he was awake at all. In fact, that almost seemed to startle her more.

"Hey," she replied, "What are you still doing up?"

"Oh, you know, I just finished watching a movie and now I'm going to clean up dinner," he said, praying that she wouldn't look over and realize there were two sets of dishes. "You're home late. Good date?"

"What? Um, yeah, yeah, it was a good date. We really, uh, connected."

"Yes, I can see that. You're lip-stick is smudged and you missed a few buttons," he paused to point at her shirt. "So you're going to see him again?"

"Yes, um, I am definitely going to see, you know…my date…again," she said as she felt the red heat rise from her chest up to her cheeks, "Anyway, I'm really beat so I'm going to head to bed. Good night."

"Good night, slutty – I mean sweetie," he said with a smirk.

Grace turned her head back toward the kitchen and stuck her tongue out at him before flashing him a smile.

As soon as he heard her bedroom door close, he ran across the apartment and burst into his room while still trying to be as quiet as possible.

"I'm sorry, I'm sorry, I'm sorry," he whispered to an obviously very annoyed Jack.

"You should be," he replied dramatically, "You really couldn't have woken me up at a more inopportune time. I was dreaming that I was at this big Hollywood party and then all of a sudden it turned into an orgy. It was me, Cher, Bette, Liza, Kevin Bacon, Bill Nye the Science Guy – "

"Jack," Will exclaimed impatiently.

"Don't worry, you were there, too."

"No, that's not – wait a minute. Did you say Bill Nye the Science Guy? Why was Bill Nye the Science Guy a part of your dream orgy?"

"You know, I don't know but I think it's best if I don't dig too deep with that one."

"Agreed," Will replied, just a bit disturbed. "But anyway, as I was saying, I'm sorry that I freaked out like that. I'm just not ready for Grace to find out about us yet," he said apologetically.

"I know. As much as I wish you were, I understand. And besides it's kind of fun to have a secret lover."

Will smiled and reached up to caress Jack's face.

"Thank you."

"You're welcome. But I'm putting it on your tab."

Will raised an eyebrow and Jack responded,

"Oh yeah, mister. You're buying me something. I don't know what it is yet, but it's going to be _big_."

"Okay," Will chuckled, "deal. Will you stay again?"

"I would love to."

As they got ready for bed, Will reflected on how far they'd come in their relationship. They laid down next to one another and after a quick goodnight kiss, they settled in for the night. Will opened his eyes once more and took in the sight of the man who had gone from being one of his best friends to the man he was now certain he was going to spend his life with and smiled with the knowledge that all of the heartache it had taken him to get to this place with Jack was worth it because it was always supposed to be him.


	3. Chapter 3

Author's Note:

It was only a matter of time before all of the secrets came spilling out ; )

Enjoy!

* * *

Chapter Three:

Day Three:

Grace was completely relaxed lying next to Karen who was snuggled up against her and using her fingers to gently trace nonsensical lines up and down Grace's arm. She let out a contented sigh and was about to drift off to sleep when she heard the sound of the front door opening.

Will had told her that he would be working late and then he was planning to go out for drinks with some friends of his and that he probably wouldn't be back until late, but she was definitely not expecting him to be this late. It was very unlike him to stay out past one o'clock on a work night, so when one thirty rolled around and there was still no sign of him, Grace had assumed that he'd met someone and gone back to his apartment. That was the only reason that she'd given into temptation and called Karen to come spend the night with her.

She knew that it was a risky move and it was very unlike her but apparently, that was the theme of the night because in a very un-him-like move, Will stayed out well into the wee hours of the morning and if the sound of a second muffled voice was any indication, he had brought someone home.

Grace's panic that she and Karen would be discovered gave way to curiosity and she tried desperately to make out the other voice, but they were speaking too quietly for her to really hear anything. As she heard Will's bedroom door slam, she convinced herself that he would be sufficiently distracted for the night and that there was no chance that he would find Karen before the morning. With a promise from Karen that she would once again leave before Will woke up in the morning, Grace allowed herself to relax and fall asleep.

* * *

Karen awoke with a bit of a start and it took her a second to figure out where she was but as soon as she heard Grace's rhythmic breathing and felt her warm body next to her, she relaxed. She looked at the clock and saw that it read 4:07 AM. Knowing how drunk Will must have been to stay out until three o'clock in the morning and then bring a total stranger back to the apartment, Karen surmised that he was probably passed out cold and that it would be safe for her to sneak into the kitchen for her midnight martini.

As soon as she entered the hallway, she heard a noise and instantly went on high alert. Grace would absolutely murder her dead if Will found her in the apartment. She ever-so-carefully snuck further into the hallway diligently listening for any other sound. Suddenly, she bumped into something and due to her already heightened state of awareness, let out a very loud yelp. Whatever it was that she had bumped into let out a similar sound only much louder and at an impossibly high pitch. Karen noted that it sounded familiar but before she even had a chance to figure out why, the light switched on and she saw Jack standing right in front of her. The two of them took in the sight of one another and let out a second yelp, which alerted both Will and Grace who came running to their doors to see what had happened.

"What's the matter," Will and Grace asked in unison.

"Jack," Grace questioned, "What are you doing here?"

"Me, um, I'm-I'm always here," Jack responded, dismissively, trying to shift focus, "The real question is why is Karen here? And why was she coming out of your room," he asked, obviously confused.

Grace was silent and as she desperately racked her brain for a plausible explanation, she felt Will and Jack staring at her waiting for an answer. Before she could come up with anything, Will jumped in and said,

"Okay, Jack, relax. Obviously, there is an explanation, which is…that…there is an explanation and it's obvious…I mean clearly…clearly…"

Will's voice trailed off and as if it were happening in slow motion, Grace sensed the wheels turning in his brain and saw in his eyes the exact moment he figured it out.

"Oh, my God! Oh, my God! What the…how the…who did…Oh, my God!"

As Grace prayed for the ground to open up and swallow her, Karen stepped forward and said,

"Alright, Nancy, before you give yourself an embolism, might I remind you that I bumped into Jack coming out of _your_ room."

Will instantly became silent and it dawned on Grace for the first time that Karen was right. Jack had come out of Will's room, where they had overheard Will take his date just over an hour ago.

"Oh, my God," Grace shrieked.

"Okay," Karen interrupted, "I got up to make a drink, so while you two do this, I'm going to go do that. Jackie, do you want me to make you my special hot cocoa?"

"Yeah," Jack replied happily as he reached out a grabbed Karen's hand.

The two of them walked over to the kitchen leaving Will and Grace standing in the hallway staring at each other in disbelief.

* * *

Will reached out and grabbed Grace's hand, dragging her into his room to the edge of his bed where he placed a hand on each of her shoulders and pushed down gently indicating that he wanted her to sit. After she was seated on his bed, he walked back over and shut the door. As he turned back around and made eye contact with her, the first thing out of his mouth was,

"Karen?"

His tone was such that it conveyed confusion, anger, disbelief, and horror.

"Jack," Grace mimicked back to him.

"Oh, please," Will said incredulously, "Don't act like my thing is anywhere near as shocking as your thing!"

"My thing," Grace said, obviously offended. "You mean my relationship?"

"Relationship," Will shouted. "What the hell are you talking about? A relationship implies a connection between two _human beings._ You're schtupping Karen, for Christ's sake."

"Whoa," Grace shouted back with her signature hand gesture. "First of all, Tevya, I am not just 'schtupping' Karen. And second of all, while I understand that me going from dating exclusively men to being in a relationship with a woman could be a bit shocking for you, it doesn't even come close to you sleeping with _Jack_ on the 'Holy-Crap-I-Did-Not-See-That-Coming Meter'. I mean my mother winning a Tony would have come closer!"

"Uh, rude! And at least Jack is a man! At least I didn't do a 180° on my sexuality and not tell my best friend."

"I didn't do a 180° on my sexuality! Maybe more like a 90°," she replied, muttering the second half under her breathe before once again raising her voice and continuing, "I haven't really figured it all out yet but on a completely separate note, congratulations on being so talented. Your ability to keep a straight face while referring to Jack as a man is truly an Oscar worthy performance."

With that Grace rose from the bed and walked passed Will to exit the room. Will, however, not ready for the argument to be over, followed her out to the living room where Karen and Jack were sitting on the couch and said,

"So, what are you telling me, Grace? That you're bi now?"

"I just said that I don't know. I haven't figured it out enough yet to put a label on it. But I am sure about Karen and me," she said confidently.

Suddenly, Jack shrieked and jumped off the couch startling everyone before dramatically crying,

"Wait a minute, wait a minute, wait a capital M-I-N lowercase u-t-e. Are you telling me that there is something going on between you and Karen?"

"Jack, you're just figuring this out now? What did you think it meant when Karen came out of Grace's bedroom in the middle of the night," an exasperated Will asked.

"I just thought they were having a sleep over," Jack said beginning to get hysterical. "Oh, dear God. You," he said pointing at Grace, "and you," he said pointing at Karen. "Eeeewwww! Oh, that is just G-R-O-double-S-gross!"

He paused as he returned to his seat on the edge of the couch and collected himself before adopting a serious face and then continued,

"Alright, as much as I don't want to know what has been going on between you two, I'm going to ask you a question and – without any details – I need you to answer with complete honesty. Has there been any, and I mean _any_ 'lesbian activity' anywhere in this apartment?"

Jack took one look at Grace's beat red face and cried,

"Oh, sweet Jesus, there has been! Alright," he said, trying, but failing miserably, to remain calm, "Well, we're going to need to call in a priest to perform the exorcism and I'm going to need Rosie to get in touch with that cousin of hers that performs the sage rituals and live animal sacrifices. We need to cleanse this place before I can ever sleep here again."

Karen, having had enough of Jack's dramatics for her current lack-of-intoxication level, piped up and said,

"Yes, Jackie, it's all true. There has been lesbian activity in this apartment. In fact, there was some of the really dirty kind right where you're sitting, about, oh, what was it, Gracie, six weeks ago?"

With that, Jack let out the sharpest of sharp shrieks and leapt off the couch into Will's arms before running toward the bathroom screaming,

"Oh, God, I need to shower and get it off me! I'll never feel clean again!"

"Well," Grace began, "that's certainly a strapping buck you've landed yourself."

"Six weeks," Will said angrily, "You've been lying to me for six weeks?"

"No, silly," Karen said in between sips of her martini, "She's been lying to you for three months."

"Karen," Grace warned, "You're really not helping."

"Three months," Will cried.

"Yes, I know it's bad. But, how long have you been lying to me," Grace asked.

"Not for three months."

"How long?"

"Two and a half months,"

"Well, that's much better."


	4. Chapter 4

Author's Note:

This is the beginning of day seven which is the final day, but it will be split up into three chapters because otherwise it would be the longest chapter of life lol.

* * *

Chapter Four:

Day Seven – Part One:

"So, tell me, honey. Have things gotten any better," Karen asked Grace as they sat in the restaurant eating lunch.

"What do you mean," Grace replied trying to sound nonchalant.

"Oh, come on, honey. I know that things have been a little off between you and Wilma since the other night and I know that it must be driving you crazy."

"Maybe a little," Grace responded quietly.

"You can talk to me about it if you'd like to, Gracie," she said as she reached across the table and placed her hand on top of Grace's, giving it a little squeeze.

"Really?"

"Of course, honey. You know what a great listener I am."

Grace raised her eyebrow and gave Karen a little smirk.

"Alright, so it hasn't been a strong suit for me in the past, but I'll give it my best shot. Talk to me, sweet cheeks," Karen said, adopting an old-timey movie accent.

"Okay," Grace began with a smile which quickly disappeared, "Well, it's just been strange, I guess. It's like, Will isn't mad at me and I'm not exactly mad at him, we just aren't talking; almost like we don't know what to say to each other. And we have _never_ had that problem before. We fight, and we yell, and we say mean things sometimes, but we always say _something_. But the last few days – silence."

"Well, what is it that you want to say to him?"

"I don't know! That's the problem; I don't know what either one of us could say to make it not awkward."

"Okay, if he can't say anything, what do you want him to do?"

"I want him to understand. Or at least try to understand. I want him to tell me that it's totally fine and completely normal and not at all crazy that I am out of the blue attracted to a woman. I want him to help me understand how that is possible. I want him to help me understand what is going on. I mean, I don't want to freak you out Karen, but I am freaking out! I don't understand how you went from being someone I essentially paid to criticize me and all of my life choices to being the first person I think about when I wake up and the last person I think about before I go to sleep. How did you become the person that gives me butterflies and sends chills down my spine? Why now, after all of these years, did I suddenly wake up one day and think to myself, 'Holy crap! If I don't kiss Karen today, I think I will implode!'? I mean, don't get me wrong, I'm so glad that it happened, I just want to understand why," Grace rambled before pausing to take a breath.

"Okay, honey, well – "

"And you know what else," Grace began again, "You know I really, really want? I want him to be happy for me. I want him to look at me and say, 'Gracie, I am so happy for you. I am happy that you found someone that knows how crazy you are and loves you anyway. I am happy that you have someone that gives you that 'dizzy, nauseous, lightheaded – but in a good way feeling' when you look at her. I am happy that you are with someone who makes your toes curl when you kiss her. I am happy that you have found the person that you really, truly love.' I want him to understand that _that_ is how you make me feel and I want him to tell me that he is happy for me."

Pausing for a second to ensure that Grace was actually finished this time, Karen said,

"Oh, Gracie, I'm sure he will get there. As much as she grinds my gears, I have to give Wilma points for loving you as much as she does. Just give it a little bit of time."

Grace nodded silently and tried to swallow the tears that had pooled in her eyes.

"I know it will happen," Karen tried again to reassure her, "and until it does – I know it's not exactly what you wanted but I'm very happy for you. I am happy that you have someone who makes you feel that way and I'm so happy that it's me because I feel the same way about you."

Grace gave Karen's hand a final squeeze and flashed her a smile that made Karen's heart clench in her chest.

"I love you, Gracie."

"I love you, too, Kare."

* * *

"I'm sorry I haven't been a very entertaining lunch date, today," Will said to Jack who sat across the table, "I'm just…I don't know," he trailed off.

"Upset because you're having a fight with the Mrs.," Jack offered sympathetically.

"That's just it, it's not really a fight. There's just been this weird, awkward tension but no real fighting has occurred – which is very unlike us."

"Well, you two need to talk, that's for sure."

"I don't know what to say. I don't think she does either."

"Okay, how about this? Why don't we do a little role playing? I'll be Grace, only with much better style and taste in men, obviously, and you be yourself," Jack said becoming more excited with each word, "You start!"

"No, Jack – "

"Jack? Who's Jack," he said dramatically flipping his head from side to side looking all over the restaurant, "There's no Jack here. I'm Grace, a thirty-something, box-dye red-headed, back stabbing, best friend stealing, basket case with a bad nose job."

"Maybe we should be using this time to work through _your_ issues with Grace," Will suggested trying to both change the subject and force Jack to confront his fear that he was going to lose Karen to Grace, which had become increasingly obvious to Will over the past few days.

"No," Jack said like a stubborn child refusing to go to bed, "Now, come on, pretend I'm Grace and talk to me."

Sensing that he would not win this battle, Will gave in and began,

"Okay, fine, I'll talk, but I'm not pretending you're Grace."

Jack shrugged and motioned to proceed with his hand.

"I just don't understand why she wouldn't tell me, you know? I'm mean her and _Karen_? That's huge! She consults me before buying a pair of underwear but the fact that she is sleeping with her female assistant, she hides. I don't get it."

"Okay, well, maybe – "

"And you know what really ticks me off," Will interrupted, "She hasn't said anything about you and me. She hasn't told me that she's happy for me, I mean, hell, even saying isn't happy about it is better than saying nothing!"

"But you really want her to be happy, don't you?"

"Yeah…I do. I mean, you and me, it's been such a long road, Jack, and I'm so happy that we ended up here. I was beginning to doubt that it existed – you know, that 'thing' that people talk about – but then you came along and…You make me happy, Jack and I just want her to be happy that I am happy."

"I know you do."

Jack stood up, walked around the table, and slid into the booth next to Will. As he put his arm around him and felt Will's head drop onto his shoulder, he said,

"I'm sure that she is happy for you – for both of us. She probably just needs a little time to process it and then I'm sure she will be ecstatic. I mean let's face it, who wouldn't be thrilled for their best friend if they landed a catch like me,"

Will wasn't 100% sure if Jack was joking about the last part or not, but he was touched by his words nonetheless. He had come to learn that Jack possessed an incredible amount of tenderness and sincerity and the moments when he chose to show it always warmed Will's heart. He leaned forward and gave Jack a kiss and said,

"Thank you, Jack."

"Anytime."


	5. Chapter 5

Chapter Five:

Day Seven – Part Two:

"Miss Karen?"

"Huh? Oh, I'm sorry, Rosie," Karen said as she snapped back into reality and took the drink that Rosario was offering her, "I was just day-dreaming I guess."

"Si, you seem to have a lot on your mind. Do you want to talk about it," Rosario asked as she sat down on the lounge opposite Karen.

"Oh, Rosie, you know me so well. I can't hide anything from you. You see, I'm worried about Gracie. She and Will are having a tough time and it's really getting her down. She's worse off than I was that time that we lost the key to the liquor storage room."

"Dios mio," Rosie said, grasping the seriousness of the situation.

"And on top of that, I'm really starting to get worried about Jackie. He's taking the news about Gracie and me much harder than I thought he would. I've offered to take him shopping every day for the past three days and he's turned me down each time."

"Well, I'm not an expert but I did complete three semesters of my Bachelor's in Psychology. I would say that the only way to help Grace is to get her to talk to Will. And as for Jack, he is acting out because he thinks that he is going to lose you now that you have found someone new. Just keep trying to reassure him that he can never be replaced, and he will calm down eventually."

"Wow, Rosie, I never realized how much you know about this kind of stuff. That really helps, thank you."

"You're welcome, Mami," Rosie said as she rose from the couch and began to walk out of the library.

"Oh, before you go," Karen began causing Rosie to turn back around to look at her, "do you think you could top off my drink Dr. Phil?"

Karen began to laugh, and Rosie turned to exit the room and muttered under her breath,

"You're going to need a doctor when I smother you in your sleep, you drunken ass."

Still laughing to herself a bit Karen rose from the lounge and began to freshen her drink when all of a sudden, inspiration struck.

* * *

Jack answered the phone and was surprised to hear Karen's voice on the other end of the line.

"Hi, Jackie, it's me."

"Hi, Kare. What's up?"

"Listen, I know that you've been really busy this week, but I was hoping that you would come stay at the manse tonight. I have your room all ready for you."

"Gee, I don't know, Kare – "

"Please, Jackie? I really miss you."

The truth was that he desperately missed her too and he wanted nothing more than to go and spend the night in his favorite place with his best friend.

"Okay, I'd love to."

"Great!"

"I should probably tell Will, though, in case he is looking for me."

"Oh, I wouldn't worry about that, honey. Will and Grace are going to be very busy tonight..."

Listening intently as Karen filled him in on her plan, he marveled once again at her evil genius and thanked his lucky stars that he very rarely found himself on her bad side.

* * *

Having spent their evening together getting manicures and massages, Jack and Karen were now getting ready to call it a night. Karen sat on the edge of Jack's bed while he lay beneath the covers, ready for her to tuck him in. As she looked down at his face, she sensed that the chance to have the discussion she had been putting off all night was either now or never, so she took a deep breath and began,

"Jackie, I want to talk to you about something…well, not just something, me and Grace."

"Karen, you really don't have to explain – "

"No, Jackie, I think I do. I really want you to understand that this thing between Grace and I is real…I love her, and I want you to be okay with that. You will always be my best friend, but I hope that you can accept that Grace is a big part of my life now, too. I know that you two have a strange relationship, but I also know that deep down you love her. So, I hope that someday, you can accept our relationship and maybe even be happy for us."

It took Jack a moment to process what she had said, and in his silence, Karen began to feel the fear that he wouldn't be able to do what she asked of him creep up on her but after a few seconds, Jack looked up and made eye contact with her,

"Does she make you happy," he asked sincerely.

"She makes me feel like I've had twelve shots of tequila, even when I've only had two," she replied, as though that were the highest compliment.

"And you really love her?"

"She's the love of my life, Jackie," Karen said, feeling the emotion and depth of those words catch in her throat.

"Okay, then," Jack said with a smile.

Karen let out a breath that she hadn't realized she was holding. Those two small words and the look on his face had lifted the burden that she had silently carried around for the past three months. She loved Grace more than she ever thought possible, but Jack was her best friend, her pal, her partner in crime, somehow both her little boy and her father – her everything. The thought of him not being okay with her relationship had bothered her more than she had been willing to admit but now that she knew that he could accept it, her heart felt lighter than she could ever remember it being.

"Hey, Kare," Jack asked tentatively.

"Yes, Poodle?"

"Who's your Daddy?"

"You are, Jackie," Karen replied with a sincere smile.

She tucked the covers all around him and lifted her hand up to gently graze his cheek before adding,

"You always will be."

His smile spoke a thousand words and Karen was relieved that he was finally sure of the place he would always hold in her heart.

"Now," she said, "is it a Judy, Liza, or Barbra kind of night?"

"Hmmm, Judy."

"Well, alright then. Goodnight, Poodle. Have sweet dreams," she said before she began to sing,

" _Somewhere over the rainbow,_

 _Way up high,_

 _There's a land that I heard of,_

 _Once in a lullaby…_ "

* * *

Grace sat on the couch watching Will pace back and forth across the living room and trying to figure out what the hell was going on. She had gotten a call from Karen telling her that there was a surprise for her in the apartment but when she'd arrived all she had found was a body guard posted outside the door who had ushered her inside where Will sat waiting for her in a state of total panic. She wracked her brain, trying to think of any reason why Karen would have done this, but she was coming up empty when out of the corner of her eye, she noticed a piece of paper sitting on the dining room table. She rose from the couch and walked across the room to pick it up and read it.

" _Hey, Red,_

 _I knew that you'd be the one to notice this letter first. Considering that your wife is a lawyer, he really isn't all that observant. Anyway, you're probably wondering why I've corralled you in this apartment with Wilma. Well, honey, as much as I don't understand why, you love him. It's important to you that he understands and accepts out relationship, so it's important to me, too._

 _P.S. I have a sneaking suspicion that he would like your understanding and acceptance of his relationship with Jack as well. So, do me a favor and be as open-minded as you can be and hear him out. The two of you are free to leave as soon as you sort out your shit and no sooner. Until then, I'll be waiting for you._

 _All my love,_

 _Karen_ "

As Grace was smiling to herself and falling in little bit more in love with Karen, Will was freaking out. He stopped pacing, turned to look at Grace, and shrieked,

"We're trapped! There is a six-foot-five, three-hundred-pound security guard posted at the door! Your bat-shit-crazy lady lover has us locked in here!"

"She's not crazy," Grace said, still smiling.

"That's all you have to say? She's not crazy? My ass, she's not crazy! She has us imprisoned. False imprisonment, that's what this is! She will rue the day, mark my words. I am going to sue her gin-soaked ass to kingdom come," he said, becoming more hysterical with each word.

"Will, you can't sue her. She's your client," Grace replied calmly.

"Oh, right," he said, clearly a bit disappointed, before inspiration struck and he continued excitedly, "No, you know what? I _am_ going to sue her and I'm going to argue both sides! Finally, I'll have a real challenge in the courtroom. I can out-lawyer everyone else in this city but can I out-lawyer myself? Ha-ha!"

"And she's the crazy one?"

"You're right," Will said, returning to reality, "I've got to get out of here. I'm going insane. What has it been – four, five hours?"

"It's been twenty minutes," Grace said trying to suppress her laughter.

"Oh, my God," he shrieked dramatically.

"Okay, relax! If you really want to get out of here then I think you should read this," she said handing him the letter.

He took the piece of paper from her and read through it quickly. As he calmed down a bit he couldn't help but smile to himself and admit that Karen was sometimes wiser than he gave her credit for; definitely certifiably insane, but wise nonetheless.

"Okay, well I do want to get out of here. I mean, I know that it's our home but something about knowing that we're locked in makes it seem claustrophobic somehow. So, I guess we should start talking."

He motioned for her to sit on the couch and as they sat facing one another they both tried to break the ice by starting,

"Okay, well…"

They both paused and tried again,

"You go…"

"Rock, paper, scissors," Will offered.

"Rock, paper, scissor, shoot…"

"Paper beats rock, you go first," Grace said.

"I don't know where to start," he said, at a loss.

"How about at the beginning?"

"That's the thing, there is no beginning. Every other relationship I have ever had, there was a definite beginning. I met someone at a club, or at a restaurant, or on a blind date and that was the beginning, but Jack has just always been there, you know? He was like this wonderful, funny, loving, guy that was always right there in front of my face and I just never saw him. And then one day, I _saw_ him, and I just knew," Will paused for a moment and Grace took note of the smile on his face and the look in his eye, "It's so easy with him. We know everything about each other and neither one of us wants the other one to change. We're comfortable and I've never had that before. I really like it."

"You really like him," Grace said, finally understanding.

"I love him," Will replied.

And with that all of Grace's confusion and apprehension melted away and all that was left was a genuine happiness for her friend.

"Okay," she said with tears in her eyes.

"Okay," he repeated hopefully.

"Okay," she nodded, "I mean, I guess it makes sense. You're right; Jack has always been there. And he was the one who helped you come out; you two have a special bond. Plus, I've always kind of thought that he had a crush on you."

"That's funny. I've always thought that Karen might have had a crush on you."

"Really?"

The thought gave Grace butterflies and Will couldn't help but notice the twinkle in her eye that his words had produced.

"Yeah," he said, "Thank you, Gracie."

He reached his hand out and grabbed ahold of hers. She gave his hand a gentle squeeze and said,

"I just want you to be happy, Will."

"I am," he smiled. "Okay, now you go. I swear, I don't mean this the way it's going to sound but, what the hell happened?"

"Oh," she sighed, "You have no idea how many times I have asked myself that question."

For the first time, Will saw Grace's true confusion and distress and he felt his heart break for her. He remembered that feeling all too well from that time in his life when he first realized that he might be a bit different from other people and he now felt a tremendous guilt for not recognizing it immediately in Grace and offering her more support and less judgement. He began to rub circles on the back of her hand as she took a deep breath and continued,

"I still don't really have an answer I guess, except that when I look at her or when she looks at me, I don't have any questions about anything. It's just right, Will. It's more right and real and wonderful than anything else I've ever had."

The look in her eye as she described her feelings for Karen told Will everything that he needed to know but he still asked,

"Are you in love with her?"

"Yes," Grace said tentatively, still afraid that he wouldn't understand.

"Is she in love with you?"

"Yes," Grace said, but this time with a smile that she couldn't contain.

"Well, then," Will said sincerely, "I am thrilled for you. Both of you."

"Really," Grace asked, feeling a wave of relief flood over her.

"Really," Will said as he leaned forward and gave her a kiss on the forehead. "All I have ever wanted was for you to find someone who loved you the way you deserve to be loved and for you to be happy."

"Thank you," Grace replied and gave him a kiss.

"I just have one thing to ask."

"Shoot."

"Why did you hide it from me," Will asked without a hint of anger or bitterness in his voice.

"Oh, God, I don't know. I guess it was just all so confusing and it felt like everything was upside down and inside out and I was so overwhelmed. I knew that if I told you about it and you freaked out, it would make it so easy for me to convince myself that it was crazy, and that I should stop it but…I just…I didn't want it to stop. So, I didn't say anything," she paused to look up at him and then added, "I'm sorry."

"It's okay, Gracie. I get it. Believe it or not, that is the same reason I didn't tell you about Jack and I'm sorry, too."

"It's okay," she nodded, "So, we're good?"

"We're good," he replied.

They sat in a comfortable silence for a few seconds before Will turned to her with a cheeky smile and said,

"So, have we made any headway on the whole 'label' thing? Are we thinking lesbian or 'just-gay-for-my-assistant'? Or you know, I'll tell you, bi is very en vogue these days."

"I don't know," she chuckled, "I guess somewhere between 'just-gay-for-my-assistant' and bi? One thing I can say for sure is that I have definitely been putting way too much emphasis on penises this whole time. Turns out that you really don't need one to have a good time."

"Speak for yourself," he said with a wink.


	6. Chapter 6

Author's Note:

This is the final chapter but if you have made it this far – THANK YOU! There were so many dynamics to try and capture in this story, so I hope that it reads true to the characters' voices and relationships. I loved writing this story so much and the there will always be a little part of me that wishes that the real show would end like this haha! Feel free to leave a review and I hope you enjoy the ending!

Also, I have a few ideas buzzing around in my head for a prequel of sorts. Kind of a "how Will & Jack/Grace & Karen got together in the first place" thing, so let me know if you'd be interested.

* * *

Chapter Six:

Day Seven – Part 3:

Rosario answered the door and found Will and Grace standing on the other side.

"We weren't expecting you so soon," she said, "Miss Karen is waiting for you up in the library."

"Thanks," they responded in unison as they entered the apartment and walked up the stairs.

As they entered the library Karen turned to look at them with a surprised expression on her face.

"Well, that was even quicker than I thought it would be. Did you two get everything all sorted out?"

"Yes, we did," Will said, "And thank you so much for trapping us in our apartment and having us guarded by an armed ex-Navy Seal. That's always something one looks forward to coming home to."

"Oh, relax, Wilma. Bodyguard looks tough but he's really just a big teddy bear! Unless you try to take my jewels or my liquor, then he'll do things to you that you never thought possible."

Will shuddered at the thought, but Grace stepped forward toward Karen and said,

"Thank you."

She placed a kiss on the brunette's lips to convey her genuine gratitude for everything she had done for her.

"You know," Will said, "I'll be honest, that is going to take me a minute to get used to."

"Oh, please, Betty Lou. That's nothing! I'll have you know that your sweet little Gracie here can be quite the dirty bird."

"Karen," Will said in a tone that he meant to be a warning, but which apparently only served to encourage her.

"I'll tell you," she began again, clearly loving watching him squirm, "for someone who lived the first thirty-three years of her life as a straight Jew from Schenectady, the things this one can do with her – "

"Karen," Will shouted.

"Shhhh! Jackie is asleep right next door! It took me all of the early recordings of Judy and half of Cher's collection of lesser known ballads to get him down," she warned.

"Alright, I'm sorry," he replied quietly, "But let's just make this clear: I am fine with you two as a couple and I am very happy for the both of you, but I do not, repeat _do not_ , want to know what goes on in your bedroom."

"How about the living room?"

"No."

"Shower?"

"No."

"Kitchen?"

"No," he said as he looked desperately at Grace who just shrugged her shoulders and tried to contain her laughter at his discomfort and annoyance.

"Limo?"

"Karen," he finally shouted.

With that, Jack stumbled into the library wearing his pajamas and rubbing his eyes.

"Well, that's great, Wilma," Karen scolded, "You woke the boy! You're putting him back to sleep this time because I'm not doing it again."

"Why is everybody here," Jack asked sleepily, "Why are Mommy and Daddy fighting?"

"Poodle," Karen said happily, "no one's fighting. The plan worked! We can be one big happy family again!"

"Can we," Jack asked dramatically as he whipped his head in Grace's direction and said coolly, "Hello, Grace."

"Hi, Jack," she responded with a smile.

"So," he paused for dramatic effect, "you're sleeping with my husband?"

"Well, Poodle," Karen interjected, "it's only fair if you think about it. You're sleeping with her wife."

She laughed nervously and tried to break the tension. Grace reached out for her hand and gave it a small squeeze to reassure her that she would make everything right. She stepped forward and stood in front of Jack.

"Jack," she began, "I know that you're upset with me because you think that I might take Karen away from you."

"Ugh, Grace," Jack said in his most annoyed tone, "that's not it at all! It's just that I'm worried that you might take Karen away from me."

Grace rolled her eyes and tried her best not to get frustrated with Jack because of his inability to listen to anyone but himself,

"Okay," she said slowly, "so, what you're saying is that you're worried that I might take Karen away from you?"

"Yes! Oh, my God, Grace! How did you get to be so insightful," he said acting more like his over-excited and over-dramatic self.

"It's a gift," she replied, dryly, before becoming serious, "But here's the thing Jack. I will never, ever try to take Karen away from you."

"You won't," he asked, sounding like a little boy.

"I won't," Grace reassured him, "I know how much you love Karen and I know how much she loves you. I could never come between the two of you and I would never want to try."

She paused to allow her words to sink in before continuing,

"It's actually kind of perfect if you think about it. Will and I could never have healthy relationships because our partners were always frustrated by our relationship with each other but you and Karen both understand because you two are exactly the same."

"Hey," Jack said, beginning to get excited, "maybe this could work. I mean, Will and I can be in a relationship and you and Karen can be in a relationship – as long as you swear on the Holiest of Holy Objects to never make me privy to any form of lesbian activity – but then you and Will and me and Karen can all have relationships of our own!"

"Exactly," Grace said as she tried to comprehend what Jack has just spit out at a mile a minute, "I think."

Jack turned to leave the room and Karen, who along with Will had watched the entire encounter with a smile on her face, said,

"Jackie, where are you going?"

"To get my Cher doll," he replied as if it were the most obvious thing in the world. "She agreed to swear on the Holiest of Holy Objects and she'd better follow through or else this whole arrangement is going to go straight down the crapper. I'm serious, if I see anything more than a quick peck on the lips, I will go full Britney circa 2007."

Jack promptly returned with his most prized possession and the Cher Doll Ceremony commenced. After it was over, they all toasted their newly found and accepted happiness with a glass of champagne before agreeing that it was late and that they should all get some sleep. Will and Grace decided that it was too late to go all the way back to their apartment and that they would just spend the night at the manse.

Goodnights, both verbal and in the form of a kiss on Will and Grace's part and a tummy-touch on Jack and Karen's, were exchanged. As they all prepared to head off to bed, Will took hold of Grace's arm causing her to look at him and said,

"This is going to work, isn't it?"

"Yeah," she replied happily, "I think it is."

They exchanged one last goodnight kiss and then each couple retired to their respective rooms, hand-in-hand, and with contented smiles on their faces.

The End


End file.
